Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What Holly Hill is known for
Holly Hill is a small mainland city on the Halifax River, wedged between Daytona Beach and Ormond Beach. It is known for its string of riverfront parks along Riverside Drive and for Pictona, a 49-court pickleball complex on Ridgewood Avenue. Local lore centers on Bill McCoy, the Prohibition rum runner behind the phrase "The Real McCoy," who once used the Sunrise Park South site.
William S. and Mary Fleming bought the Fitch land grant in 1875 and named the settlement Holly Hill after the Fleming family home in Holywood, Ireland. Residents voted to incorporate on July 2, 1901, partly to deal with hogs getting into gardens, and cigar factory owner Frank "Vet" Cave became the first mayor. The McCoy family arrived in 1898, and their home at LPGA Boulevard and Riverside Drive still stands. Holly Hill is a quiet, older, mostly residential town with riverfront walking paths, modest single-family streets and several manufactured home communities. Residents get Daytona Beach convenience at a lower price point, with Sunday farmers market mornings and pickleball as the social glue.
Where to live
One of Holly Hill's most active residential areas for home sales, with single-family homes on established streets. (source)
An established single-family neighborhood that sees steady resale activity. The Riviera Oaks Dog Park on Alabama Avenue sits nearby. (source)
Riverfront condominium community on the Halifax River. The city's Riverside Park was built through a 2007 land swap with Marina Grande. (source)
The road that runs along the Halifax River, lined with city parks, piers and boat ramps. Homes and condos here trade on river views and water access. (source)
A manufactured home community in Holly Hill, one of the more affordable ways to own in town. (source)
A manufactured home community in Holly Hill offering lower-cost housing options. (source)
Local favorites
Chef Mayra Rodriguez's Spanish-style octopus, beef tenderloin with chimichurri and sticky toffee pudding. Small room, reservations recommended. (source)
Scratch-made Cuban sandwiches, pork tenderloin sandwiches with hand-cut fries and brisket plates. (source)
Baby back ribs, sliced and pulled pork sandwiches and homemade Brunswick stew. (source)
Small family-run spot known for pad Thai, red curry, fresh rolls and mango sticky rice. (source)
Long-running family pizzeria and sub shop. Locals order the homemade meatball sub and the Sorrento's Special. (source)
Neighborhood takeout that regulars have used for decades, known for egg rolls and General Tso chicken. (source)
Fried pork chunk plates with rice, black beans and plantains, plus chicharron. (source)
The full-service restaurant inside Pictona, where players grab food, beer and wine between games. (source)
After hours
Small craft brewery on 2nd Street with its own beers, a courtyard, live music and visiting food trucks. (source)
Family-owned distillery on N Beach Street making sugarcane vodka and rum, with free tours and tastings. (source)
Irish pub on Ridgewood Avenue serving haddock, scotch eggs and bangers alongside its beers. (source)
Pool hall on N Nova Road with nine-foot tables, including two pro-level tables, plus food and drinks. Open at the same spot for more than 35 years. (source)
Casual neighborhood bar on Flomich Street with a fire pit, outdoor TVs and steak nights. Busy during Daytona Bike Week. (source)
Shopping
Weekly Sunday market held at Sunrise Park North on the riverfront. (source)
Hundreds of vendor booths on Tomoka Farms Road, open Friday through Sunday year-round, with produce, crafts and monthly classic car cruises. (source)
Shopping, dining and movie theater district across from Daytona International Speedway, with free parking. (source)
Historic downtown core with local shops, a farmers market and riverfront Cassen Park. (source)
Outdoors
Riverfront park with a 1.5 mile walking path, an outdoor fitness court, a large playground, a fishing pier and pavilions overlooking the Halifax River. (source)
1.35 acres on the Halifax River with a boat ramp, kayak launch and pavilions. Bill McCoy once ran his rum-running operation from this site. (source)
Free riverfront park on Riverside Drive with a fishing pier and restrooms. (source)
Fenced dog park on Alabama Avenue with separate small and large dog areas, water, shade and a pond. (source)
Former Native American site with lagoons, a boat ramp, canoe rentals, camping and more than 160 bird species recorded. (source)
Undeveloped barrier island beaches, dunes and Mosquito Lagoon, with ancient Timucua shell mounds. The Apollo Beach entrance is the closest access. (source)
Things to do
49-court pickleball complex with 13 covered courts, a stadium that also hosts concerts, a restaurant, putting green and shuffleboard. Open to day-pass players. (source)
Volunteer-run museum on Ridgewood Avenue with artifacts from early Holly Hill and Daytona. Free admission. (source)
Restored World War I era boxcar at City Hall, one of 49 sent by France in 1949 as thanks for American food aid. (source)
Home of the DAYTONA 500 and Rolex 24, with daily guided tours that end at the Motorsports Hall of Fame of America. (source)
Florida's tallest lighthouse at 175 feet, built in 1887 and now a National Historic Landmark with keeper's dwellings to tour. (source)
On the calendar
Free, no-ticket evening celebration at Sunrise Park marking 125 years since incorporation. (source)
NASCAR's season-opening race at Daytona International Speedway. The 2027 race is set for February 21. (source)
Ten-day motorcycle rally across the Daytona area. The 2027 dates are March 5 to 14. (source)
Downtown riverfront festival run by Ormond Beach MainStreet, scheduled for November 21 and 22, 2026. (source)
Schools
Holly Hill School K-5
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
US 1 (Ridgewood Avenue), Nova Road (SR 5A), LPGA Boulevard and nearby I-95
Daytona Beach International Airport, about 15 min; Orlando International Airport, about 1 hr 10 min
Ryan C. Winslow, broker/owner of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Researched and verified 2026-09-28. Businesses change; call ahead.